[1R-(1α,2β,3α,4β,5α)]-N-[2,3,4,5-tetrahydroxy-2-(hydroxymethyl)cyclopentyl]-N'-[2,3,4-tris-O-(phenylmethyl)-α-D-glucopyranosyl]thiourea

Base Information

• Chemical Name: [1R-(1α,2β,3α,4β,5α)]-N-[2,3,4,5-tetrahydroxy-2-(hydroxymethyl)cyclopentyl]-N'-[2,3,4-tris-O-(phenylmethyl)-α-D-glucopyranosyl]thiourea
• CAS No.: 172909-55-6
• Molecular Formula: C₃₄H₄₂N₂O₁₀S
• Molecular Weight: 670.781
• Mol file: 172909-55-6.mol

Synonyms:[1R-(1α,2β,3α,4β,5α)]-N-[2,3,4,5-tetrahydroxy-2-(hydroxymethyl)cyclopentyl]-N'-[2,3,4-tris-O-(phenylmethyl)-α-D-glucopyranosyl]thiourea

Chemical Property of [1R-(1α,2β,3α,4β,5α)]-N-[2,3,4,5-tetrahydroxy-2-(hydroxymethyl)cyclopentyl]-N'-[2,3,4-tris-O-(phenylmethyl)-α-D-glucopyranosyl]thiourea

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [1R-(1α,2β,3α,4β,5α)]-N-[2,3,4,5-tetrahydroxy-2-(hydroxymethyl)cyclopentyl]-N'-[2,3,4-tris-O-(phenylmethyl)-α-D-glucopyranosyl]thiourea

There total 18 articles about [1R-(1α,2β,3α,4β,5α)]-N-[2,3,4,5-tetrahydroxy-2-(hydroxymethyl)cyclopentyl]-N'-[2,3,4-tris-O-(phenylmethyl)-α-D-glucopyranosyl]thiourea which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

trehazolamine (151061-97-1) + tri-O-benzyl-α-D-glucose isothiocyanate (172909-54-5) → [1R-(1α,2β,3α,4β,5α)]-N-[2,3,4,5-tetrahydroxy-2-(hydroxymethyl)cyclopentyl]-N'-[2,3,4-tris-O-(phenylmethyl)-α-D-glucopyranosyl]thiourea (172909-55-6)

Guidance literature:

In N,N-dimethyl-formamide; for 24h;

DOI:10.1021/jo980485y

Reference yield:

benzyl chloride (100-44-7) → [1R-(1α,2β,3α,4β,5α)]-N-[2,3,4,5-tetrahydroxy-2-(hydroxymethyl)cyclopentyl]-N'-[2,3,4-tris-O-(phenylmethyl)-α-D-glucopyranosyl]thiourea (172909-55-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent

2: 50 percent / BF₃*Et₂O / toluene / 48 h / 23 °C

3: pyridine / dimethylformamide

With pyridine; boron trifluoride diethyl etherate; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00152a026

Reference yield:

1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose (10548-46-6) → [1R-(1α,2β,3α,4β,5α)]-N-[2,3,4,5-tetrahydroxy-2-(hydroxymethyl)cyclopentyl]-N'-[2,3,4-tris-O-(phenylmethyl)-α-D-glucopyranosyl]thiourea (172909-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / BF₃*Et₂O / toluene / 48 h / 23 °C

2: pyridine / dimethylformamide

With pyridine; boron trifluoride diethyl etherate; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00152a026

upstream raw materials:

trehazolamine

tri-O-benzyl-α-D-glucose isothiocyanate

2,3-di-O-benzyl-4,6-O-benzylidene-D-glucopyranose

(2R,4aR,6S,7R,7aS)-6,7-Bis-benzyloxy-4a-hydroxy-2-phenyl-tetrahydro-cyclopenta[1,3]dioxin-5-one O-methyl-oxime

Downstream raw materials:

trehazolin

(3aR,4R,5S,6S,6aS)-4-Hydroxymethyl-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-ylamino)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazole-4,5,6-triol